Benzoyl isothiocyanate → HCID 9886701, compound

HRID 2257084Notes

Reaction equation

HRID 2257084 reaction equation
[Na+].[C:2]([C:5]1[C:14](=[O:15])[C:13]2[C:8](=[CH:9][C:10]([N:17]3[CH2:22][CH2:21][N:20](N=CSCC4CSC5N(C(=O)C5NC(=O)CC5SC=CC=5)C=4C([O-])=O)[CH2:19][CH2:18]3)=[C:11]([F:16])[CH:12]=2)[N:7]([CH:48]2[CH2:50][CH2:49]2)[CH:6]=1)([OH:4])=[O:3].C([N:59]=[C:60]=[S:61])(=O)C1C=CC=CC=1.C1C2C(=O)C(C(O)=O)=CN(C3CC3)C=2C=C(N2CCNCC2)C=1F.[Na]>C1COCC1>[NH2:59][C:60](=[S:61])[N:20]1[CH2:19][CH2:18][N:17]([C:10]2[CH:9]=[C:8]3[C:13]([C:14](=[O:15])[C:5]([C:2]([OH:4])=[O:3])=[CH:6][N:7]3[CH:48]3[CH2:49][CH2:50]3)=[CH:12][C:11]=2[F:16])[CH2:22][CH2:21]1

Participants

5

Reactant 3

HCID 68284Benzoyl isothiocyanateHCID 6723330993107-09-6HCID 131720110HCID 131720110, compound

Product 1

HCID 9886701HCID 9886701, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
41 fahrenheit

Procedure

R-[6a,7b]]-3-[[[(3-Carboxy-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-quinolinyl)-4-piperazinyl]iminomethyl]thio methyl]-8-oxo-7-[(2-thienylacetyl)amino]-5-thia-1-azabicyclo [4.2.0]oct-2-ene-2-carboxylic acid sodium salt, of the following formula ##STR332## according to this invention, is made as follows. A solution of benzoyl isothiocyanate (0.92 g) in THF (20 ml) is added to a mixture of ciprofloxacin sodium salt (2.0 g) in THF (300 ml), and the reaction is stirred for 20 hours. The reaction is concentrated to dryness and the residue is triturated with acetone. The resultant benzoylurea is added to a preheated at approximately 80° C. (176° F.) solution of 5% aqueous NaOH and the reaction is stirred for 30 minutes. The mixture is cooled to approximately 5° C. (41° F.) and acidified with 1N HCl. The solid is collected by filtration and recrystallized from DMF to yield 7-[4-(aminothioxomethyl)-1-piperazinyl]-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid.

Workup

  1. concentrationThe reaction is concentrated to dryness
  2. customthe residue is triturated with acetone
  3. additionThe resultant benzoylurea is added to
  4. customa preheated at approximately 80° C.
  5. custom(176° F.) solution of 5% aqueous NaOH
  6. stirringthe reaction is stirred for 30 minutes
  7. filtrationThe solid is collected by filtration
  8. customrecrystallized from DMF

Sources & evidence

ORD record
ord-4da9b4197bbd418db36d85a3ccb92ee0
Source dataset
uspto-grants-1997_08
Patent number
US05656623

Reaction notes

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